Silicone hydrogel composition, silicone hydrogel lens, and method of manufacturing silicone hydrogel lens

ABSTRACT

A silicone hydrogel composition includes a first hydrophilic monomer, a siloxane compound, a first crosslinking monomer, a second hydrophilic monomer, and a second crosslinking monomer. The first hydrophilic monomer and the siloxane compound have an acrylate group or an acrylamide group and may also have a methacrylate group or a methacrylamide group. The first crosslinking monomer has a plurality of acrylate groups or acrylamide groups and may also have methacrylate groups or methacrylamide groups. The second hydrophilic monomer has a non-conjugated vinyl group. The second crosslinking monomer has a plurality of non-conjugated vinyl groups. A sum of the weight of the second hydrophilic monomer and the weight of the second crosslinking monomer is 40 to 100 parts by weight, relative to 100 parts by weight of the sum of the weight of the first hydrophilic monomer, the weight of the siloxane compound, and the weight of the first crosslinking monomer.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to Taiwan Application Serial Number107143129, filed Nov. 30, 2018, which is herein incorporated byreference.

BACKGROUND Field of Invention

The present disclosure relates to a silicone hydrogel composition, asilicone hydrogel lens made from the silicone hydrogel composition, anda method of manufacturing the silicone hydrogel lens.

Description of Related Art

With the increasing popularity of contact lenses, wearing comfort of acontact lenses has been increasingly valued by wearers. Siliconehydrogel contact lenses have high oxygen permeability since they includea siloxane compound. Sufficient oxygen can pass directly through thelens and contact cornea to provide sufficient oxygen—to the cornea.Accordingly, even if a silicone hydrogel contact lens is worn for a longtime, it is less likely to cause symptoms of eye discomfort due tocorneal hypoxia.

However, the manufacturing cost of a silicone hydrogel contact lens ismuch more expensive than that of a contact lens excluding a siloxanecompound. It is because in the manufacture of a silicone hydrogelcontact lens, the lens should be washed using an organic solvent such asisopropanol, ethanol or methyl ethyl ketone to remove unreacted siloxanecompound. Therefore, how to reduce the manufacturing cost of a siliconehydrogel contact lens is still an urgent problem to be solved.

SUMMARY

An aspect of the present disclosure provides a silicone hydrogelcomposition including a first hydrophilic monomer, a siloxane compound,a first crosslinking monomer, a second hydrophilic monomer, and a secondcrosslinking monomer. Each of the first hydrophilic monomer and thesiloxane compound has an acrylate group or an acrylamide group and mayalso have a minor amount of a methacrylate group or a methacrylamidegroup. The first crosslinking monomer has a plurality of acrylate groupsor acrylamide groups and may also have methacrylate groups ormethacrylamide groups. The second hydrophilic monomer has anon-conjugated vinyl group. The second crosslinking monomer has aplurality of non-conjugated vinyl groups. A sum of the weight of thesecond hydrophilic monomer and the weight of the second crosslinkingmonomer is 40 to 100 parts by weight, relative to 100 parts by weight ofa sum of the weight of the first hydrophilic monomer, the weight of thesiloxane compound, and the weight of the first crosslinking monomer.

In one embodiment of the present disclosure, energy required for thepolymerization of the second hydrophilic monomer and the secondcrosslinking monomer is higher than that of the first hydrophilicmonomer, the siloxane compound, and the first crosslinking monomer.

In one embodiment of the present disclosure, the siloxane compound is ina range of 35 wt % to 60 wt % based on the total weight of the siliconehydrogel composition.

In one embodiment of the present disclosure, the siloxane compound has astructure of the following formula (1):

in which X is O or NH;L is (CH₂)_(m), (CH₂)_(m)—[O(CH₂)_(p)]_(q) or(CH₂)_(m)(CHOH)—[O(CH₂)_(p)]_(q);R₁ is OH, CH₃ or OSi(CH₃)₃;R₂ is CH₃ or OSi(CH₃)₃;R₃ is an alkyl group;n is an integer from 1 to 30;m and p are integers from 2 to 5; andq is an integer from 1 to 5.

In one embodiment of the present disclosure, the siloxane compound is asiloxane monomer, a siloxane macromonomer or a siloxane prepolymer.

In one embodiment of the present disclosure, the siloxane compound has anumber average molecular weight of less than 1200.

In one embodiment of the present disclosure, the siloxane compound isselected from the group comprising 3-tris(trimethyl siloxy) silylpropylacrylamide, 3-tris(trimethyl siloxy) silylpropyl acrylate,3-tris(triethyl siloxy) silylpropyl acrylamide, 3-tris(triethyl siloxy)silylpropyl acrylate, (3-acryloxy-2-hydroxy propoxy) propylbis(trimethyl siloxy) methyl silane, (3-acryloxy-2-hydroxy propoxy)propyl bis(trimethyl siloxy) ethyl silane, (3-acrylamido-2-hydroxypropoxy) propyl bis(trimethyl siloxy)methyl silane,(3-acrylamido-2-hydroxy propoxy) propyl bis(trimethyl siloxy)ethylsilane, α-acrylamidopropyl-ω-butyl polydimethylsiloxane,α-acrylamidoethoxypropyl-ω-butyl polydimethylsiloxane,α-acryloxybutyl-ω-butyl polydimethylsiloxane, α-acryloxypropyl-ω-butylpolydimethylsiloxane, α-acryloxyethoxypropyl-ω-butylpolydimethylsiloxane, bis-α,ω-acrylamidopropyl polydimethylsiloxane,bis-α,ω-acrylamidoethoxypropyl polydimethylsiloxane,bis-α,ω-acryloxybutyl polydimethylsiloxane, bis-α,ω-acryloxypropylpolydimethylsiloxane, bis-α,ω-acryloxyethoxypropyl polydimethylsiloxane,or a combination thereof.

In one embodiment of the present disclosure, the first hydrophilicmonomer is in a range of 10 wt % to 40 wt % based on the total weight ofthe silicone hydrogel composition.

In one embodiment of the present disclosure, the first hydrophilicmonomer is selected from the group comprising 2-hydroxyethyl acrylamide,glycerol acrylate, acrylic acid, N,N-dimethylacrylamide, hydroxyethylacrylamide, 2-acrylamido-2-methylpropanesulfonic acid, or a combinationthereof.

In one embodiment of the present disclosure, the first crosslinkingmonomer is in a range of 0.1 wt % to 5 wt % based on the total weight ofthe silicone hydrogel composition.

In one embodiment of the present disclosure, the first crosslinkingmonomer is selected from the group comprising trimethylpropyltrimethacrylate, ethylene glycol diacrylate, diethylene glycoldiacrylate, triethylene glycol diacrylate, trimethylolpropanetriacrylate, pentaerythritol tetra acrylate, tetraethylene glycoldiacrylate, ethylene diacrylamide, butylene 1,4-diacrylamide, or acombination of thereof.

In one embodiment of the present disclosure, the second hydrophilicmonomer is in a range of 20 wt % to 50 wt % based on the total weight ofthe silicone hydrogel composition.

In one embodiment of the present disclosure, the second hydrophilicmonomer is selected from the group comprising N-vinyl pyrrolidone,1-vinylazonan-2-one, N-vinyl-N-methyl acetamide, vinyl sulfonic acid,glycine vinyl carbamate, glycine vinyl carbonate, or a combinationthereof.

In one embodiment of the present disclosure, the second crosslinkingmonomer is in a range of 0.01 wt % to 1 wt % based on the total weightof the silicone hydrogel composition.

In one embodiment of the present disclosure, the second crosslinkingmonomer is 1,3,5-triallyl isocyanurate.

In one embodiment of the present disclosure, the first hydrophilicmonomer, the siloxane compound, and the first crosslinking monomerinclude acrylate groups or acrylamide groups. Those may also include aminor amount of methacrylate groups or methacrylamide groups. When thoseinclude methacrylate groups or methacrylamide groups, those are in arange of less than or equal to 20 wt % based on the total weight of thesilicone hydrogel composition.

In an embodiment of the present disclosure, the silicone hydrogelcomposition further includes a photoinitiator.

In one embodiment of the present disclosure, the photoinitiator isselected from the group comprising 1-hydroxycyclohexyl phenyl ketone,2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1,2,2-dimethoxy-1,2-diphenylethan-1-one, bis(η5,2,4-cyclo pentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrol-1-yl)-phenyl)titanium,2,4,6-trimethyl benzoyl diphenyl phosphine oxide, phenylbis(2,4,6-trimethyl benzoyl)phosphine oxide, bis-(2,6-dimethoxy benzoyl)(2,4,4-trimethylpentyl) phosphine oxide or a combination thereof.

Another aspect of the present disclosure provides a silicone hydrogellens made from a silicone hydrogel composition described above using aphotocuring reaction.

In one embodiment of the present disclosure, the silicone hydrogel lensis free of extraction using an organic solvent after the photocuringreaction.

Another aspect of the present disclosure provides a method ofmanufacturing a silicone hydrogel lens including: (i) providing asilicone hydrogel composition as described above; and (ii) sequentiallyperforming a first photocuring reaction and a second photocuringreaction on the silicone hydrogel composition to form the siliconehydrogel lens, in which energy applied in the second photocuringreaction is higher than energy applied in the first photocuringreaction.

In an embodiment of the present disclosure, the energy applied in thefirst photocuring reaction is less than 50 mJ/cm², and the energyapplied in the second photocuring reaction is higher than 100 mJ/cm².

In an embodiment of the present disclosure, after performing the firstphotocuring reaction and the second photocuring reaction, the methodfurther includes: (iii) extracting the silicone hydrogel lens using anaqueous solution.

The above description will be described in detail in the followingembodiments, and further explanation of the technical solutions of thepresent disclosure will be provided.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a graph showing the relationship between the curing ratio andthe time of the silicone hydrogel compositions according to someembodiments of the present disclosure.

DETAILED DESCRIPTION

In order that the present disclosure is described in detail andcompleteness, implementation aspects and specific embodiments of thepresent disclosure with illustrative description are presented; but itis not the only form for implementation or use of the specificembodiments. The embodiments disclosed herein may be combined orsubstituted with each other in an advantageous manner, and otherembodiments may be added to an embodiment without further description.In the following description, numerous specific details will bedescribed in detail in order to enable the reader to fully understandthe following embodiments. However, the embodiments of the presentdisclosure may be practiced without these specific details.

Silicone Hydrogel Composition

The silicone hydrogel composition of the present disclosure can be usedto prepare a silicone hydrogel contact lens (hereinafter referred to asa contact lens). According to various embodiments, the silicone hydrogelcomposition includes a first hydrophilic monomer, a siloxane compound, afirst crosslinking monomer, a second hydrophilic monomer, and a secondcrosslinking monomer. Preferably, in one embodiment, a sum of the weightof the second hydrophilic monomer and the weight of the secondcrosslinking monomer is 40 to 100 parts by weight, relative to 100 partsby weight of a sum of the weight of the first hydrophilic monomer, theweight of the siloxane compound, and the weight of the firstcrosslinking monomer. For example, a sum of the first hydrophilicmonomer, the siloxane compound, and the first crosslinking monomer is ina range of 50 wt % to 80 wt % based on the total weight of the siliconehydrogel composition, and a sum of the second hydrophilic monomer andthe second crosslinking monomer is in a range of 20 wt % to 50 wt %based on the total weight of the silicone hydrogel composition.

First Hydrophilic Monomer

According to various embodiments, the first hydrophilic monomer has anacrylate group

a methacrylate group

an acrylamide group

or a methacrylamide group

Preferably, in one embodiment, the first hydrophilic monomer is in arange of 15 wt % to 30 wt % based on the total weight of the siliconehydrogel composition. In some embodiments, the first hydrophilic monomeris selected from the group comprising 2-hydroxyethyl methacrylate(HEMA), 2-hydroxyethyl acrylamide (HEAA), glycerol acrylate, acrylicacid, N,N-dimethylacrylamide (DMA), hydroxyethyl acrylamide,2-acrylamido-2-methylpropanesulfonic acid, or a combination thereof.

Siloxane Compound

According to various embodiments, the siloxane compound has an acrylategroup, a methacrylate group, an acrylamide group, or a methacrylamidegroup. In one embodiment, the siloxane compound refers to a compoundhaving a plurality of repeating dimethylsiloxane groups, and thecompound further has at least one acrylate group, methacrylate group,acrylamide group or methacrylamide group. In one embodiment, thesiloxane compound is a compound having at least two repeatingdimethylsiloxane groups, and the compound further has at least twoacrylate groups, methacrylate groups, acrylamide groups ormethacrylamide groups.

In one embodiment, the siloxane compound has a structure of thefollowing formula (1):

in which X is O or NH; L is (CH₂)_(m), (CH₂)_(m)—[O(CH₂)_(p)]_(q) or(CH₂)_(m)(CHOH)—[O(CH₂)_(p)]_(q); R₁ is OH, CH₃ or OSi(CH₃)₃; R₂ is CH₃or OSi(CH₃)₃; R₃ is an alkyl group; n is an integer from 1 to 30; m andp are integers from 2 to 5; and q is an integer from 1 to 5.

In one embodiment, the siloxane compound is a siloxane monomer, asiloxane macromonomer or a siloxane prepolymer. Preferably, in oneembodiment, the siloxane compound is in a range of 35 wt % to 60 wt %based on the total weight of the silicone hydrogel composition. In someembodiments, the siloxane compound is selected from the group comprising3-tris(trimethyl siloxy) silylpropyl acrylamide (TRISAm),3-tris(trimethyl siloxy) silylpropyl acrylate (TRISA), 3-tris(triethylsiloxy) silylpropyl acrylamide, 3-tris(triethyl siloxy) silylpropylacrylate, (3-acryloxy-2-hydroxy propoxy) propyl bis(trimethyl siloxy)methyl silane, (3-acryloxy-2-hydroxy propoxy) propyl bis(trimethylsiloxy) ethyl silane, (3-acrylamido-2-hydroxy propoxy) propylbis(trimethyl siloxy)methyl silane, (3-acrylamido-2-hydroxy propoxy)propyl bis(trimethyl siloxy)ethyl silane, α-acrylamidopropyl-ω-butylpolydimethylsiloxane, α-acrylamidoethoxypropyl-ω-butylpolydimethylsiloxane, α-acryloxybutyl-ω-butyl polydimethylsiloxane,α-acryloxypropyl-ω-butyl polydimethylsiloxane,α-acryloxyethoxypropyl-ω-butyl polydimethylsiloxane,bis-α,ω-acrylamidopropyl polydimethylsiloxane,bis-α,ω-acrylamidoethoxypropyl polydimethylsiloxane,bis-α,ω-acryloxybutyl polydimethylsiloxane, bis-α,ω-acryloxypropylpolydimethylsiloxane, bis-α,ω-acryloxyethoxypropyl polydimethylsiloxane,or a combination thereof. In some embodiments, the siloxane compound hasa number average molecular weight (Mn) of less than 1200, such as in arange of 200 to 1200. Preferably, in one embodiment, the siloxanecompound has a number average molecular weight of less than 1000, suchas less than 800.

First Crosslinking Monomer

According to various embodiments, the first crosslinking monomer has aplurality of acrylate groups, methacrylate groups, acrylamide groups, ormethacrylamide groups. Preferably, in one embodiment, the firstcrosslinking monomer is in a range of 0.1 wt % to 5 wt % based on thetotal weight of the silicone hydrogel composition. In some embodiments,the first crosslinking monomer is selected from the group comprisingtrimethylpropyl trimethacrylate (TMPTMA), ethylene glycol diacrylate,diethylene glycol diacrylate, triethylene glycol diacrylate,trimethylolpropane triacrylate, pentaerythritol tetra acrylate,tetraethylene glycol diacrylate, ethylene diacrylamide, butylene1,4-diacrylamide, or a combination of thereof.

It should be understood that each of the first hydrophilic monomer, thesiloxane compound, and the first crosslinking monomer includes anacrylate group or an acrylamide group and may also include a minoramount of a methacrylate group or a methacrylamide group to providespecific technical effects, as described in more detail below.

Second Hydrophilic Monomer

According to various embodiments, the second hydrophilic monomer has anon-conjugated vinyl group. Preferably, in one embodiment, the secondhydrophilic monomer is in a range of 20 wt % to 50 wt % based on thetotal weight of the silicone hydrogel composition. In some embodiments,the second hydrophilic monomer is selected from the group comprisingN-vinyl pyrrolidone, 1-vinylazonan-2-one, N-vinyl-N-methyl acetamide,vinyl sulfonic acid, glycine vinyl carbamate, glycine vinyl carbonate,or a combination thereof.

Second Crosslinking Monomer

According to various embodiments, the second crosslinking monomer has aplurality of non-conjugated vinyl groups. Preferably, in one embodiment,the second crosslinking monomer is in a range of 0.01 wt % to 1 wt %based on the total weight of the silicone hydrogel composition. In someembodiments, the second crosslinking monomer is 1,3,5-triallylisocyanurate (TAIC).

As described above, each of the first hydrophilic monomer, the siloxanecompound, and the first crosslinking monomer includes an acrylate groupor an acrylamide group and may also include a minor amount of amethacrylate group or a methacrylamide group to provide specifictechnical effects. Specifically, compared to a compound having anon-conjugated vinyl group (e.g., the second hydrophilic monomer and thesecond crosslinking monomer), a compound having an acrylate group, anacrylamide group, a methacrylate group or a methacrylamide group haslower energy required for polymerization. Therefore, when the siliconehydrogel composition of the present disclosure is cured, low energy maybe firstly applied to polymerize the first hydrophilic monomer, thesiloxane compound, and the first crosslinking monomer. After those arecompletely polymerized, high energy is applied to polymerize the secondhydrophilic monomer and the second crosslinking monomer.

According to this, when a low energy is applied, the second hydrophilicmonomer and the second crosslinking monomer have not started topolymerize, and the first hydrophilic monomer, the siloxane compound,and the first crosslinking monomer have already been completelypolymerized to form a network. Next, when a high energy is applied, thesecond hydrophilic monomer and the second crosslinking monomer arepolymerized on the formed network to form an interpenetrating polymernetwork (IPN). Since almost all of the siloxane compound has beencompletely polymerized without residue after the end of the curingreaction, it is not necessary to use an organic solvent to wash the lensobtained by polymerization, thereby reducing the manufacturing cost ofthe contact lens.

However, it should be noted that the first hydrophilic monomer, thesiloxane compound, and the first crosslinking monomer may include amethacrylate group, but steric hindrance of the methacrylate groupenhances the energy required for the polymerization of these compounds.Therefore, preferably, in the silicone hydrogel composition, the firsthydrophilic monomer, the siloxane compound, and the first crosslinkingmonomer having the methacrylate group are not too many, so that thesecompounds can be polymerized when low energy is applied. For example,the first hydrophilic monomer, the siloxane compound, and the firstcrosslinking monomer including the methacrylate group are less than orequal to 20 wt % based on the total weight of the silicone hydrogelcomposition, such as 18 wt %, 15 wt %, 10% or 5 wt %.

Photoinitiator

According to various embodiments, the silicone hydrogel compositionfurther includes a photoinitiator. In some embodiments, thephotoinitiator is selected from the group comprising 1-hydroxycyclohexylphenyl ketone (hereinafter referred to as 1-184),2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1,2,2-dimethoxy-1,2-diphenylethan-1-one, bis(η5,2,4-cyclo pentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrol-1-yl)-phenyl)titanium),2,4,6-trimethyl benzoyl diphenyl phosphine oxide (hereinafter referredto as TPO), phenyl bis(2,4,6-trimethyl benzoyl)phosphine oxide(hereinafter referred to as 1-819), bis-(2,6-dimethoxy benzoyl)(2,4,4-trimethylpentyl) phosphine oxide (hereinafter referred to as1-403), or a combination thereof, such as Irgacure-1800 (hereinafterreferred to as 1-1800, which is a combination of 1-403 and 1-184) orIrgacure 1700 (hereinafter referred to as 1-1700, which is a combinationof 1-403 and Darocur 1173 (hereinafter referred to as D-1173)). D-1173is 2-hydroxy-2-methyl propiophenone.

Manufacture of Silicone Hydrogel Lens

According to various embodiments, a method of manufacturing a siliconehydrogel lens includes sequentially performing a first photocuringreaction and a second photocuring reaction on the silicone hydrogelcomposition. Specifically, the silicone hydrogel composition is filledinto a cavity of a polypropylene mold to perform the first photocuringreaction and the second photocuring reaction. In detail, the energyapplied in the second photocuring reaction is higher than the energyapplied in the first photocuring reaction. In one embodiment, the energyapplied in the first photocuring reaction is higher than the energyrequired for the polymerization of the first hydrophilic monomer, thesiloxane compound, and the first crosslinking monomer in the siliconehydrogel composition and lower than the energy required for thepolymerization of the second hydrophilic monomer and the secondcrosslinking monomer. The energy applied in the second photocuringreaction is higher than the energy required for the polymerization ofthe second hydrophilic monomer and the second crosslinking monomer. Insome embodiments, the energy applied in the first photocuring reactionis less than 50 mJ/cm², such as 40 mJ/cm², 30 mJ/cm², or 20 mJ/cm². Insome embodiments, the energy applied in the second photocuring reactionis greater than 100 mJ/cm², such as 110 mJ/cm², 120 mJ/cm², or 130mJ/cm².

In one embodiment, the method of manufacturing the silicone hydrogellens further includes extracting the silicone hydrogel lens using anaqueous solution after performing the first photocuring reaction and thesecond photocuring reaction. Since the water-insoluble siloxane compoundhas been completely polymerized without residue, the obtainedpolymerized lens can be washed only using the aqueous solution toextract unreacted other components (e.g., the second hydrophilic monomeror the second crosslinking monomer).

Extraction of Silicone Hydrogel Lens

Extraction of the silicone hydrogel lens of the present disclosureincludes extraction of the silicone hydrogel lens using water, methanol,and isopropanol. Specifically, extracting the silicone hydrogel lensusing methanol or isopropanol includes obtaining the cured siliconehydrogel lens from a polypropylene mold and measuring a first weight ofthe silicone hydrogel lens. Subsequently, the silicone hydrogel lens isextracted with methanol or isopropanol at 45° C. for 2 hours.Thereafter, the silicone hydrogel lens is dried in an oven at 70° C. for16 hours, and a second weight of the silicone hydrogel lens is measured.The difference (%) in weight between the first weight and the secondweight is the weight of the methanol extracts or the isopropanolextracts.

Extracting the silicone hydrogel lens using water includes obtaining thecured silicone hydrogel lens from a polypropylene mold and measuring afirst weight of the silicone hydrogel lens. Subsequently, the siliconehydrogel lens is extracted with water at 80° C. for 2 hours. Thereafter,the silicone hydrogel lens is dried in an oven at 70° C. for 16 hours,and a second weight of the silicone hydrogel lens is measured. Thedifference (%) in weight between the first weight and the second weightis the weight of the water extracts.

The following embodiments and comparative embodiments are used todescribe in detail the silicone hydrogel composition and the method ofmanufacturing the silicone hydrogel lens (hereinafter, simply referredto as “lens” for convenience of explanation) and the effects thereof.However, the following embodiments are not intended to limit the presentdisclosure.

Comparison of Curing Reactions of Silicone Hydrogel CompositionsContaining Different Photoinitiators Embodiment 1-1 to Embodiment 1-9

40 parts by weight of α-acrylamidopropyl-ω-butyl polydimethylsiloxane(having a number average molecular weight of less than 800), 25 parts byweight of N,N-dimethylacrylamide, 5 parts by weight of 2-hydroxyethylmethacrylate, 0.4 parts by weight of trimethylpropyltrimethacrylate, and5 parts by weight of tert-amyl alcohol were mixed to form a siliconehydrogel composition. The above silicone hydrogel composition wasdivided into nine equal portions, and different photoinitiators listedin Table 1 below were added to the portions, respectively.

Next, the silicone hydrogel composition to which the photoinitiator wasadded was filled into cavities of polypropylene molds, and the curingreactions were carried out under ultraviolet light with differentenergies and illumination times. The curing results are listed in Table1.

TABLE 1 parts by illumination weight of UV energy time curing Embodimentphotoinitiator photoinitiator (mJ/cm²) (min) ratio 1-1 D-1173 0.3 150300 uncured 1-2 250 240 uncured 1-3 TPO 0.3 150 10 100% 1-4 0.1 30 20100% 1-5 I-819 0.3 150 5 100% 1-6 0.1 30 10 100% 1-7 I-184 0.1 30 120 85% 1-8 I-1800 0.1 30 120  85% 1-9 I-1700 0.1 30 60  50%

As can be seen from Table 1, when 1-819, TPO, 1-184, 1-1800, and 1-1700were used as photoinitiators, the silicone hydrogel compositions couldbe cured with ultraviolet light of lower energy (30 mJ/cm²). Inparticular, when 0.1 parts by weight of 1-819 was used as thephotoinitiator, the silicone hydrogel composition could be completelycured within 10 minutes of illumination, and when 0.1 parts by weight ofTPO was used as the photoinitiator, the silicone hydrogel compositioncould be completely cured within 20 minutes of illumination. Further,when 0.3 parts by weight of 1-819 was used as the photoinitiator, thesilicone hydrogel composition could be completely cured within 5 minutesof illumination, and when 0.3 parts by weight of TPO was used as thephotoinitiator, the silicone hydrogel composition could be completelycured within 10 minutes of illumination.

When I-184, I-1800 or I-1700 were used as the photoinitiators, thesilicone hydrogel compositions required more than 60 minutes ofillumination to be completely cured. However, when D-1173 was used asthe photoinitiator, the silicone hydrogel composition could not be curedeven if ultraviolet light of extremely high energy (150 and 250 mJ/cm²)was applied.

Comparison of Curing Rates of Hydrogel Composition ContainingNon-Conjugated Vinyl Monomer and Silicone Hydrogel CompositionContaining Acrylamide Monomer Embodiment 2

40 parts by weight of N-vinyl pyrrolidone, 0.1 parts by weight of1,3,5-triallyl isocyanurate, and 5 parts by weight of tert-amyl alcoholwere mixed to form a hydrogel composition. Next, 0.1 parts by weight ofTPO was added as a photoinitiator and thoroughly mixed.

Next, the hydrogel composition of Embodiment 2 to which thephotoinitiator was added was filled in a cavity of a polypropylene mold,and ultraviolet light of 30 mJ/cm² was applied to carry out a curingreaction. The relationship between the curing ratio and the time of thesilicone hydrogel compositions of Embodiments 1-4 and 2 is shown in FIG.1 .

As can be seen from FIG. 1 , compared to the hydrogel composition ofEmbodiment 2 (including the non-conjugated vinyl monomer such as N-vinylpyrrolidone), the silicone hydrogel composition of Embodiment 1-4(including the acrylamide-based monomer such as N,N-dimethylacrylamide)had higher curing rate. Specifically, the curing ratio of the siliconehydrogel composition of Embodiment 1-4 had reached about 90% before thehydrogel composition of Embodiment 2 began to cure. Therefore, when thesilicone hydrogel compositions of Embodiment 1-4 and Embodiment 2 weremixed and subjected to a curing reaction, most of the acrylamide-basedmonomer had been cured before the non-conjugated vinyl monomer began tocure. When the non-conjugated vinyl monomer (e.g., N-vinyl pyrrolidone)began to cure, a majority of the siloxane compound such asα-acrylamidopropyl-ω-butyl polydimethylsiloxane had been completelycured, so that the unreacted siloxane compound which need to be furtherremoved was insignificant.

Preparation of Lens Including Non-Conjugated Vinyl Monomer andAcrylamide-Based Monomer Embodiment 3-1

40 parts by weight of α-acrylamidopropyl-ω-butyl polydimethylsiloxane(siloxane compound 1), 25 parts by weight of N,N-dimethylacrylamide(DMA), 5 parts by weight of 2-hydroxyethyl methacrylate (HEMA), 30 partsby weight of N-vinyl pyrrolidone (NVP), 0.4 parts by weight oftrimethylpropyl trimethacrylate (TMPTMA), 0.1 parts by weight of1,3,5-triallyl isocyanurate (TAIC), 0.2 parts by weight of TPOphotoinitiator, 0.02 parts by weight of a blue colorant (RB-19), and 5parts by weight of tert-amyl alcohol were mixed to form a siliconehydrogel composition. Next, the silicone hydrogel composition was filledinto a cavity of a polypropylene mold, and ultraviolet light of 30mJ/cm² was applied for 6 minutes to carry out a first photocuringreaction. Subsequently, ultraviolet light of 132 mJ/cm² was applied for6 minutes to carry out a second photocuring reaction to form a lens.

Embodiment 3-2

In this embodiment, the same components as in Embodiment 3-1 in additionto 5 parts by weight of HEMA replaced by 5 parts by weight of2-hydroxyethyl acrylamide (HEAA), and 0.4 parts by weight of TMPTMAreplaced by 0.4 parts by weight of ethylene glycol diacrylate(bisacrylate (2)), and 0.2 parts by weight of TPO photoinitiatorreplaced by 0.1 parts by weight of TPO photoinitiator were mixed to forma silicone hydrogel composition. Next, the silicone hydrogel compositionwas filled into a cavity of a polypropylene mold, and ultraviolet lightof 30 mJ/cm² was applied for 4 minutes to carry out a first photocuringreaction. Subsequently, ultraviolet light of 132 mJ/cm² was applied for4 minutes to carry out a second photocuring reaction to form a lens.

Embodiment 3-3

In this embodiment, the same components as in Embodiment 3-2 in additionto 5 parts by weight of tert-amyl alcohol replaced by 10 parts by weightof tert-amyl alcohol were mixed to form a silicone hydrogel composition.Next, the silicone hydrogel composition was filled into a cavity of apolypropylene mold, and ultraviolet light of 30 mJ/cm² was applied for 4minutes to carry out a first photocuring reaction. Subsequently,ultraviolet light of 132 mJ/cm² was applied for 4 minutes to carry out asecond photocuring reaction to form a lens.

Embodiment 3-4

50 parts by weight of α-acrylamidopropyl-ω-butyl polydimethylsiloxane(siloxane compound 1), 25 parts by weight of N,N-dimethylacrylamide(DMA), 5 parts by weight of 2-hydroxyethyl acrylamide (HEAA), 20 partsby weight of N-vinyl pyrrolidone (NVP), 0.6 parts by weight of ethylenediacrylamide (bisacrylamide (2)), 0.1 parts by weight of 1,3,5-triallylisocyanurate (TAIC), 0.15 parts by weight of TPO photoinitiator, 0.02parts by weight of a blue colorant (RB-19), and 15 parts by weight oftert-amyl alcohol were mixed to form a silicone hydrogel composition.Next, the silicone hydrogel composition was filled into a cavity of apolypropylene mold, and ultraviolet light of 30 mJ/cm² was applied for 6minutes to carry out a first photocuring reaction. Subsequently,ultraviolet light of 132 mJ/cm² was applied for 6 minutes to carry out asecond photocuring reaction to form a lens.

Embodiment 3-5

In this embodiment, the same components as in Embodiment 3-4 in additionto 0.6 parts by weight of ethylene diacrylamide (bisacrylamide (2))replaced by 0.6 parts by weight of ethylene glycol diacrylate(bisacrylate (2)), and 0.15 parts by weight of TPO photoinitiatorreplaced by 0.1 parts by weight of TPO photoinitiator were mixed to forma silicone hydrogel composition. Next, the silicone hydrogel compositionwas filled into a cavity of a polypropylene mold, and ultraviolet lightof 30 mJ/cm² was applied for 8 minutes to carry out a first photocuringreaction. Subsequently, ultraviolet light of 132 mJ/cm² was applied for8 minutes to carry out a second photocuring reaction to form a lens.

Embodiment 3-6

In this embodiment, the same components as in Embodiment 3-4 in additionto 0.15 parts by weight of TPO photoinitiator replaced by 0.1 parts byweight of the TPO photoinitiator were mixed to form a silicone hydrogelcomposition. Next, the silicone hydrogel composition was filled into acavity of a polypropylene mold, and ultraviolet light of 30 mJ/cm² wasapplied for 8 minutes to carry out a first photocuring reaction.Subsequently, ultraviolet light of 132 mJ/cm² was applied for 8 minutesto carry out a second photocuring reaction to form a lens.

Embodiment 3-7

In this embodiment, the same components as in Embodiment 3-5 in additionto 0.6 parts by weight of ethylene glycol diacrylate (bisacrylate (2))replaced by 0.4 parts by weight of pentaerythritol tetra acrylate(tetraacrylate (4)) were mixed to form a silicone hydrogel composition.Next, the silicone hydrogel composition was filled into a cavity of apolypropylene mold, and ultraviolet light of 30 mJ/cm² was applied for 8minutes to carry out a first photocuring reaction. Subsequently,ultraviolet light of 132 mJ/cm² was applied for 8 minutes to carry out asecond photocuring reaction to form a lens.

Next, the lenses of Embodiments 3-1 to 3-7 were taken out from thepolypropylene molds, and the lenses were extracted with water andisopropanol according to the methods described above to obtain weightsof water extracts and weights of isopropanol extracts.

Further, oxygen permeability, elongation, and refractive index of thelenses of Embodiments 3-1 to 3-7 were measured. The oxygen permeabilitywas obtained by placing the lens in a phosphorate buffered saline andmeasuring using a polarographic method. Detailed procedures formeasuring the oxygen permeability are known in the art and will not bedescribed herein. Dk is usually acted as a unit of the oxygenpermeability, and 1Dk=10⁻¹¹ (cm³ O₂ cm)/(cm³ sec mmHg). The elongationwas measured by a tensile method. The refractive index was measuredusing an Abbe's refractometer. The water and isopropanol extractionresults, oxygen permeability, elongation, and refractive index of thelenses of Embodiments 3-1 to 3-7 are listed in Tables 2 and 3 below.

TABLE 2 Embodiment 3-1 3-2 3-3 3-4 siloxane compound 1 40   40   40   50DMA 25   25   25   25 HEMA 5   HEAA 5   5    5 NVP 30   30   30   20TMPTMA (3) 0.4 bisacrylate (2) 0.4 0.4 tetraacrylate (4) bisacrylamide(2)   0.6 TAIC 0.1 0.1 0.1   0.1 TPO 0.2 0.1 0.1    0.15 RB-19  0.02 0.02  0.02    0.02 tert-amyl alcohol 5   5   10   15 UV energy (mJ/cm²) 30→132  30→132  30→132  30→132 time (min) 6→6 4→4 4→4 6→6 weight ratioof water 2.52% 1.41% 0.33% 1.43% extracts weight ratio of 8.23% 5.13%2.85% 1.08% isopropanol extracts oxygen permeability (Dk) 56.68 46.5245.49   51.7 elongation (%)  312%  260%  334%  247% refractive index/%water  1.395 1.4011/58%   1.4035     1.4240 clarity 10   10   10   10

TABLE 3 Embodiment 3-5 3-6 3-7 siloxane compound 1 50   50   50   DMA25   25   25   HEMA HEAA 5   5   5   NVP 20   20   20   TMPTMA (3)bisacrylate (2) 0.6 tetraacrylate (4) 0.4 bisacrylamide (2) 0.6 TAIC 0.10.1 0.1 TPO 0.1 0.1 0.1 RB-19  0.02  0.02  0.02 tert-amyl alcohol 15  15   15   UV energy (mJ/cm²)  30→132  30→132  30→132 time (min) 8→8 8→88→8 weight ratio of water 0.80% 0.67% 0.47% extracts weight ratio of1.80% 1.46% 1.84% isopropanol extracts oxygen permeability (Dk) 54.9555.92 50.93 elongation (%) 276% 214% 283% refractive index/% water1.4175/50% 1.4203/48% 1.4167/50% clarity 10   10   10  

As can be seen from Tables 2 and 3, the lenses made from the siliconehydrogel compositions of the present disclosure were all opticallytransparent. Further, the lenses made from the silicone hydrogelcompositions of the present disclosure had elongations of more than200%, and thus had flexibility and elasticity suitable for use incontact lenses.

It is worth mentioning that the weight ratios of the isopropanolextracts of the lenses made using the silicone hydrogel compositions ofthe present disclosure were low, so that the produced lenses do not needto be washed using an organic solvent. However, it should be noted thatthe weight ratios of the water extracts and those of the isopropanolextracts of Embodiments 3-2 to 3-7 were similar (less than 4%), but theweight ratio of the water extracts and that of the isopropanol extractsof Embodiment 3-1 were significantly different (about 5.7%). It wasbecause the silicone hydrogel composition of Embodiment 3-1 included thehydrophilic monomer having the methacrylate group (i.e., HEMA) and thecrosslinking monomer having the methacrylate group (i.e., TMPTMA). Sincesteric hindrances of the methacrylate groups increased the energyrequired for the polymerization of these compounds, the residualisopropanol extracts were increased after the silicone hydrogelcomposition was cured.

Preparation of Lens Including Ionic Monomer Embodiment 4-1

45 parts by weight of α-acrylamidopropyl-ω-butyl polydimethylsiloxane(siloxane compound 1), 25 parts by weight of N,N-dimethylacrylamide(DMA), 5 parts by weight of 2-hydroxyethyl acrylamide (HEAA), 25 partsby weight of N-vinyl pyrrolidone (NVP), 0.6 parts by weight of ethyleneglycol diacrylate (bisacrylate (2)), 0.1 parts by weight of1,3,5-triallyl isocyanurate (TAIC), 0.1 parts by weight of TPOphotoinitiator, 0.02 parts by weight of a blue colorant (RB-19), and 15parts by weight of tert-amyl alcohol were mixed to form a siliconehydrogel composition. Next, the silicone hydrogel composition was filledinto a cavity of a polypropylene mold, and ultraviolet light of 30mJ/cm² was applied for 8 minutes to carry out a first photocuringreaction. Subsequently, ultraviolet light of 120 mJ/cm² was applied for8 minutes to carry out a second photocuring reaction to form a lens.

Embodiment 4-2

In this embodiment, the same components as in Embodiment 4-1 in additionto additionally added 1 part by weight of acrylic acid were mixed toform a silicone hydrogel composition. Next, the silicone hydrogelcomposition was filled into a cavity of a polypropylene mold, andultraviolet light of 30 mJ/cm² was applied for 8 minutes to carry out afirst photocuring reaction. Subsequently, ultraviolet light of 120mJ/cm² was applied for 8 minutes to carry out a second photocuringreaction to form a lens.

Embodiment 4-3

In this embodiment, the same components as in Embodiment 4-2 in additionto 25 parts by weight of NVP replaced by 30 parts by weight of NVP weremixed to form a silicone hydrogel composition. Next, the siliconehydrogel composition was filled into a cavity of a polypropylene mold,and ultraviolet light of 30 mJ/cm² was applied for 8 minutes to carryout a first photocuring reaction. Subsequently, ultraviolet light of 120mJ/cm² was applied for 8 minutes to carry out a second photocuringreaction to form a lens.

Next, the lenses of Embodiments 4-1 to 4-3 were taken out from thepolypropylene molds, and the lenses were extracted with water andisopropanol according to the methods described above to obtain weightsof water extracts and those of isopropanol extracts. Further, oxygenpermeability, elongation, and refractive index of the lenses ofEmbodiments 4-1 to 4-3 were measured. The water and isopropanolextraction results, oxygen permeability, elongation, and refractiveindex of the lenses of Embodiments 4-1 to 4-3 are listed in Table 4below.

TABLE 4 Embodiment 4-1 4-2 4-3 siloxane compound 1 45 45 40 DMA 25 25 25HEAA  5  5  5 NVP 25 25 30 bisacrylate (2)   0.6   0.6   0.6 acrylicacid  1  1 TAIC   0.1   0.1   0.1 TPO   0.1   0.1   0.1 RB-19    0.02   0.02    0.02 tert-amyl alcohol 15 15 15 UV energy (mJ/cm²)  30→120 30→120  30→120 time (min) 8→8 8→8 8→8 weight ratio of water 1.76% 2.13%1.07% extracts weight ratio of 2.08% 3.50% 1.43% isopropanol extractsoxygen permeability 61 62 60 (Dk) elongation (%)  276%  344%  270%refractive index/     1.4083     1.4200     1.4072 % water clarity 10 1010

As can be seen from Table 4, the lenses made from the silicone hydrogelcompositions with or without the ionic monomer (i.e., acrylic acid) hadelongations of more than 250% and were all optically transparent. Inaddition, the weight ratios of the isopropanol extracts of the lensesmade from the silicone hydrogel compositions were low and similar to theweight ratios of the water extracts (less than 1.4%). That is, thesilicone hydrogel compositions including the ionic monomer were alsosuitable for the preparation of contact lenses.

Preparation of Lenses Including Different Crosslinking MonomersEmbodiment 5-1

40 parts by weight of α-acrylamidopropyl-ω-butyl polydimethylsiloxane(siloxane compound 1), 25 parts by weight of N,N-dimethylacrylamide(DMA), 5 parts by weight of 2-hydroxyethyl acrylamide (HEAA), 30 partsby weight of N-vinyl pyrrolidone (NVP), 1.2 parts by weight of ethyleneglycol diacrylate (bisacrylate (2)), 1 part by weight of acrylic acid,0.1 parts by weight of 1,3,5-triallyl isocyanurate (TAIC), 0.1 parts byweight of TPO photoinitiator, 0.02 parts by weight of a blue colorant(RB-19) and 15 parts by weight of tert-amyl alcohol were mixed to form asilicone hydrogel composition. Next, the silicone hydrogel compositionwas filled into a cavity of a polypropylene mold, and ultraviolet lightof 30 mJ/cm² was applied for 8 minutes to carry out a first photocuringreaction. Subsequently, ultraviolet light of 132 mJ/cm² was applied for8 minutes to carry out a second photocuring reaction to form a lens.

Embodiment 5-2

In this embodiment, the same components as in Embodiment 5-1 in additionto 1.2 parts by weight of ethylene glycol diacrylate (bisacrylate (2))replaced by 0.8 parts by weight of trimethylolpropane triacrylate(triacrylate (3)) were mixed to form a silicone hydrogel composition.Next, the silicone hydrogel composition was filled into a cavity of apolypropylene mold, and ultraviolet light of 30 mJ/cm² was applied for 8minutes to carry out a first photocuring reaction. Subsequently,ultraviolet light of 132 mJ/cm² was applied for 8 minutes to carry out asecond photocuring reaction to form a lens.

Embodiment 5-3

In this embodiment, the same components as in Embodiment 5-1 were mixedto form a silicone hydrogel composition. Next, the silicone hydrogelcomposition was filled into a cavity of a polypropylene mold, andultraviolet light of 10 mJ/cm² was applied for 10 minutes to carry out afirst photocuring reaction. Subsequently, ultraviolet light of 120mJ/cm² was applied for 10 minutes to carry out a second photocuringreaction to form a lens.

Embodiment 5-4

In this embodiment, the same components as in Embodiment 5-2 were mixedto form a silicone hydrogel composition. Next, the silicone hydrogelcomposition was filled into a cavity of a polypropylene mold, andultraviolet light of 10 mJ/cm² was applied for 8 minutes to carry out afirst photocuring reaction. Subsequently, ultraviolet light of 120mJ/cm² was applied for 8 minutes to carry out a second photocuringreaction to form a lens.

Next, the lenses of Embodiments 5-1 to 5-4 were taken out from thepolypropylene molds, and the lenses were extracted using isopropanolaccording to the method described above to obtain weights of isopropanolextracts. Further, oxygen permeability, elongation, and refractive indexof the lenses of Embodiments 5-1 to 5-4 were measured. The isopropanolextraction results, oxygen permeability, elongation, and refractiveindex of the lenses of Embodiments 5-1 to 5-4 are listed in Table 5below.

TABLE 5 Embodiment 5-1 5-2 5-3 5-4 siloxane compound 1 40   40   40  40   DMA 25   25   25   25   HEAA 5   5   5   5   NVP 30   30   30  30   bisacrylate (2) 1.2 1.2 triacrylate (3) 0.8 0.8 acrylic acid 1  1   1   1   TAIC 0.1 0.1 0.1 0.1 TPO 0.1 0.1 0.1 0.1 RB-19  0.02  0.02 0.02  0.02 tert-amyl alcohol 15   15   15   15   UV energy (mJ/cm²) 30→132  30→132  10→120  10→120 time (min) 8→8 8→8 10→10 8→8 weightratio of 3.07% 5.90% 1.47% 0.30% isopropanol extracts oxygenpermeability 66.32 66.79 not not (Dk) measured measured elongation (%) 150%  268%  168%  215% refractive index   1.4064   1.4040   1.4072  1.4034

As can be seen from Table 5, when the first photocuring reaction wasperformed on the same silicone hydrogel composition using a lowerultraviolet light energy, the weight ratio of the isopropanol extractsof the produced lens could be lowered. Further, compared Embodiment 5-1with Embodiment 5-3 and compared Embodiment 5-2 with Embodiment 5-4, itwas understood that changing the ultraviolet light energy for performingthe photocuring reaction did not affect the properties such aselongation and refractive index of the formed lens.

Curing of Silicone Hydrogel Compositions Under Different ConditionsEmbodiment 6-1

40 parts by weight of α-acrylamidopropyl-ω-butyl polydimethylsiloxane(siloxane compound 1), 25 parts by weight of N,N-dimethylacrylamide(DMA), 5 parts by weight of 2-hydroxyethyl acrylamide (HEAA), 30 partsby weight of N-vinyl pyrrolidone (NVP), 0.6 parts by weight of ethyleneglycol diacrylate (bisacrylate (2)), 1 part by weight of acrylic acid,0.1 parts by weight of 1,3,5-triallyl isocyanurate (TAIC), 0.1 parts byweight of TPO photoinitiator, 0.02 parts by weight of a blue colorant(RB-19) and 15 parts by weight of tert-amyl alcohol were mixed to form asilicone hydrogel composition. Next, the silicone hydrogel compositionwas filled into a cavity of a polypropylene mold, and photocuringreactions were carried out using a lens manufacturing apparatus. Thelens manufacturing apparatus was set to sequentially apply ultravioletlight of 30 mJ/cm² for 4 minutes, ultraviolet light of 225 mJ/cm² for 4minutes, ultraviolet light of 300 mJ/cm² of for 2 minutes, andultraviolet light of 470 mJ/cm² for 2 minutes to form a lens.

Embodiment 6-2

In this embodiment, the same components as in Embodiment 6-1 in additionto 40 parts by weight of the siloxane compound 1 replaced by 45 parts byweight of the siloxane compound 1, and 30 parts by weight of NVPreplaced by 25 parts by weight of NVP were mixed to form a siliconehydrogel composition. Next, the silicone hydrogel composition was filledinto a cavity of a polypropylene mold, and photocuring reactions werecarried out using the lens manufacturing apparatus to form a lens. Thesetting of the lens manufacturing apparatus was the same as that ofEmbodiment 6-1.

Embodiment 6-3

In this embodiment, the same components as in Embodiment 6-1 were mixedto form a silicone hydrogel composition. Next, the silicone hydrogelcomposition was filled into a cavity of a polypropylene mold, andultraviolet light of 30 mJ/cm² was applied for 8 minutes to carry out afirst photocuring reaction. Subsequently, ultraviolet light of 132mJ/cm² was applied for 8 minutes to carry out a second photocuringreaction to form a lens.

Embodiment 6-4

In this embodiment, the same components as in Embodiment 6-2 were mixedto form a silicone hydrogel composition. Next, the silicone hydrogelcomposition was filled into a cavity of a polypropylene mold, andultraviolet light of 30 mJ/cm² was applied for 8 minutes to carry out afirst photocuring reaction. Subsequently, ultraviolet light of 132mJ/cm² was applied for 8 minutes to carry out a second photocuringreaction to form a lens.

Embodiment 6-5

In this embodiment, the same components as in Embodiment 6-1 were mixedto form a silicone hydrogel composition. Next, the silicone hydrogelcomposition was filled into a cavity of a polypropylene mold, andultraviolet light of 15 mJ/cm² was applied for 8 minutes to carry out afirst photocuring reaction. Subsequently, ultraviolet light of 160mJ/cm² was applied for 8 minutes to carry out a second photocuringreaction to form a lens.

Embodiment 6-6

In this embodiment, the same components as in Embodiment 6-2 were mixedto form a silicone hydrogel composition. Next, the silicone hydrogelcomposition was filled into a cavity of a polypropylene mold, andultraviolet light of 15 mJ/cm² was applied for 8 minutes to carry out afirst photocuring reaction. Subsequently, ultraviolet light of 160mJ/cm² was applied for 8 minutes to carry out a second photocuringreaction to form a lens.

Next, the lenses of Embodiments 6-1 to 6-6 were taken out from thepolypropylene molds, and the lenses were extracted using water,methanol, and isopropanol according to the methods described above toobtain weights of water extracts, those of methanol extracts and thoseof isopropanol extracts. Further, a diameter, base curve, oxygenpermeability, elongation, and refractive index of the lenses ofEmbodiments 6-1 to 6-6 were measured. The water, methanol, andisopropanol extraction results, diameter, base curve, oxygenpermeability, elongation, and refractive index of the lenses ofEmbodiments 6-1 to 6-6 are listed in Tables 6 and 7 below.

TABLE 6 Embodiment 6-1 6-2 6-3 6-4 siloxane compound 1 40 45 40 45 DMA25 25 25 25 HEAA  5  5  5  5 NVP 30 25 30 25 bisacrylate (2)   0.6   0.6  0.6   0.6 acrylic acid  1  1  1  1 TAIC   0.1   0.1   0.1   0.1 TPO  0.1   0.1   0.1   0.1 RB-19    0.02    0.02    0.02    0.02 tert-amylalcohol 15 15 15 15 curing method lens lens non-lens non-lensmanufacturing manufacturing manufacturing manufacturing apparatusapparatus apparatus apparatus UV energy (mJ/cm²)  30→225→300→470 30→225→300→470  30→132  30→132 time (min) 4→4→2→2 4→4→2→2 8→8 8→8weight ratio of 0.60% 0.30% 0.81% 1.10% water extracts weight ratio of1.09% 1.31% 1.21% 1.74% methanol extracts weight ratio of 2.00% 1.50%2.32% 2.90% isopropanol extracts diameter (mm)   14.3   14.0   14.49  14.15 base curve (mm)    8.57    8.43    8.50    8.30 oxygenpermeability (Dk) not measured not measured not measured not measuredelongation (%)  300%  280%  290%  307% refractive index     1.4016    1.4070     1.4040     1.4060

TABLE 7 Embodiment 6-5 6-6 siloxane compound 1 40   45   DMA 25   25  HEAA 5   5   NVP 30   25   bisacrylate (2) 0.6 0.6 acrylic acid 1   1  TAIC 0.1 0.1 TPO 0.1 0.1 RB-19  0.02  0.02 tert-amyl alcohol 15   15  curing method non-lens non-lens manufacturing manufacturing apparatusapparatus UV energy (mJ/cm²)  15→160  15→160 time (min) 8→8 8→8 weightratio of water 0.79% 1.13% extracts weight ratio of methanol extractsweight ratio of 2.61% 2.84% isopropanol extracts diameter (mm) 14.7914.2  base curve (mm)  8.54  8.14 oxygen permeability (Dk) 66.24 74.29elongation (%)  213%  352% refractive index   1.4019   1.4067

It can be seen from Table 6 and Table 7 that when the lens manufacturingapparatus was used to cure the silicone hydrogel compositions, theweight ratios of the water extracts and the weight ratios of theisopropanol extracts were both 2% or less, indicating that the siliconehydrogel compositions were completely cured. Further, the weight ratiosof the water extracts, those of the methanol extracts, and those of theisopropanol extracts of the lenses of Embodiments 6-1 to 6-6 were low(lower than or equal to 2.9%) regardless of whether or not the lensmanufacturing apparatus for curing the silicone hydrogel compositionswas used.

Comparison of Lens Properties of Siloxane Compounds Containing DifferentNumber Average Molecular Weights Embodiment 7-1

40 parts by weight of α-acrylamidopropyl-ω-butyl polydimethylsiloxane(number average molecular weight of about 1000, siloxane compound 2), 25parts by weight of N,N-dimethylacrylamide (DMA), 5 parts by weight of2-hydroxyethyl acrylamide (HEAA), 30 parts by weight of N-vinylpyrrolidone (NVP), 0.6 parts by weight of ethylene glycol diacrylate(bisacrylate (2)), 1 part by weight of acrylic acid, 0.1 parts by weightof 1,3,5-triallyl isocyanurate (TAIC), 0.1 parts by weight of TPOphotoinitiator, 0.02 parts by weight of a blue colorant (RB-19) and 15parts by weight of tert-amyl alcohol were mixed to form a siliconehydrogel composition. Next, the silicone hydrogel composition was filledinto a cavity of a polypropylene mold, and ultraviolet light of 35mJ/cm² was applied for 4 minutes to carry out a first photocuringreaction. Subsequently, ultraviolet light of 133 mJ/cm² was applied for4 minutes to perform a second photocuring reaction to form a lens.

Embodiment 7-2

In this embodiment, the same components as in Embodiment 7-1 in additionto 40 parts by weight of the siloxane compound 2 replaced by 40 parts byweight of α-acrylamidopropyl-ω-butyl polydimethylsiloxane (numberaverage molecular weight of less than 800, siloxane compound 1) weremixed to form a silicone hydrogel composition. Next, the siliconehydrogel composition was filled into a cavity of a polypropylene mold,and ultraviolet light of 35 mJ/cm² was applied for 4 minutes to carryout a first photocuring reaction. Subsequently, ultraviolet light of 133mJ/cm² was applied for 4 minutes to perform a second photocuringreaction to form a lens.

Embodiment 7-3

In this embodiment, the same components as in Embodiment 7-1 in additionto 40 parts by weight of the siloxane compound 2 replaced by 40 parts byweight of α-acryloxypropyl-ω-butyl polydimethylsiloxane (number averagemolecular weight of about 820, siloxane compound 3), and 0.1 parts byweight of TPO photoinitiator replaced by 0.3 parts by weight of TPOphotoinitiator, and 15 parts by weight of tert-amyl alcohol replaced by5 parts by weight of tert-amyl alcohol were mixed to form a siliconehydrogel composition. Next, the silicone hydrogel composition was filledinto a cavity of a polypropylene mold, and ultraviolet light of 30mJ/cm² was applied for 8 minutes to carry out a first photocuringreaction. Subsequently, ultraviolet light of 132 mJ/cm² was applied for8 minutes to perform a second photocuring reaction to form a lens.

Embodiment 7-4

In this embodiment, the same components as in Embodiment 7-3 in additionto no acrylic acid was added were mixed to form a silicone hydrogelcomposition. Next, the silicone hydrogel composition was filled into acavity of a polypropylene mold, and ultraviolet light of 30 mJ/cm² wasapplied for 8 minutes to carry out a first photocuring reaction.Subsequently, ultraviolet light of 132 mJ/cm² was applied for 8 minutesto carry out a second photocuring reaction to form a lens.

Embodiment 7-5

In this embodiment, the same components as in Embodiment 7-3 in additionto 25 parts by weight of DMA replaced by 20 parts by weight of DMA, and5 parts by weight of HEAA replaced by 10 parts by weight of HEAA weremixed to form a silicone hydrogel composition. Next, the siliconehydrogel composition was filled into a cavity of a polypropylene mold,and ultraviolet light of 30 mJ/cm² was applied for 8 minutes to carryout a first photocuring reaction. Subsequently, ultraviolet light of 132mJ/cm² was applied for 8 minutes to carry out a second photocuringreaction to form a lens.

Embodiment 7-6

In this embodiment, the same components as in Embodiment 7-5 in additionto no acrylic acid was added were mixed to form a silicone hydrogelcomposition. Next, the silicone hydrogel composition was filled into acavity of a polypropylene mold, and ultraviolet light of 30 mJ/cm² wasapplied for 10 minutes to carry out a first photocuring reaction.Subsequently, ultraviolet light of 132 mJ/cm² was applied for 10 minutesto carry out a second photocuring reaction to form a lens.

Embodiment 7-7

In this embodiment, the same components as in Embodiment 7-1 in additionto 40 parts by weight of the siloxane compound 2 replaced by 40 parts byweight of bis-α,ω-acryloxypropyl polydimethylsiloxane (number averagemolecular weight of about 1200, siloxane compound 4) were mixed to forma silicone hydrogel composition. Next, the silicone hydrogel compositionwas filled into a cavity of a polypropylene mold, and ultraviolet lightof 30 mJ/cm² was applied for 4 minutes to carry out a first photocuringreaction. Subsequently, ultraviolet light of 132 mJ/cm² was applied for4 minutes to carry out a second photocuring reaction to form a lens.

Embodiment 7-8

In this embodiment, the same components as in Embodiment 7-7 in additionto 40 parts by weight of the siloxane compound 4 replaced by 5 parts byweight of the siloxane compound 4, and additionally added 35 parts byweight of the siloxane compound 1 were mixed to form a silicone hydrogelcomposition. Next, the silicone hydrogel composition was filled into acavity of a polypropylene mold, and ultraviolet light of 30 mJ/cm² wasapplied for 6 minutes to carry out a first photocuring reaction.Subsequently, ultraviolet light of 132 mJ/cm² was applied for 6 minutesto carry out a second photocuring reaction to form a lens.

Embodiment 7-9

In this embodiment, the same components as in Embodiment 7-8 in additionto 35 parts by weight of the siloxane compound 1 replaced by 35 parts byweight of the siloxane compound 2 were mixed to form a silicone hydrogelcomposition. Next, the silicone hydrogel composition was filled into acavity of a polypropylene mold, and ultraviolet light of 30 mJ/cm² wasapplied for 6 minutes to carry out a first photocuring reaction.Subsequently, ultraviolet light of 132 mJ/cm² was applied for 6 minutesto carry out a second photocuring reaction to form a lens.

Embodiment 7-10

In this embodiment, the same components as in Embodiment 7-8 in additionto 35 parts by weight of the siloxane compound 1 replaced by 30 parts byweight of the siloxane compound 1, and 25 parts by weight of DMAreplaced by 30 parts by weight of DMA were mixed to form a siliconehydrogel composition. Next, the silicone hydrogel composition was filledinto a cavity of a polypropylene mold, and ultraviolet light of 30mJ/cm² was applied for 4 minutes to carry out a first photocuringreaction. Subsequently, ultraviolet light of 132 mJ/cm² was applied for4 minutes to carry out a second photocuring reaction to form a lens.

Next, the lenses of Embodiments 7-1 to 7-10 were taken out from thepolypropylene molds, and the lenses were extracted with water andisopropanol according to the methods described above to obtain weightsof water extracts and those of isopropanol extracts. Further, adiameter, base curve, oxygen permeability, elongation, and refractiveindex of the lenses of Embodiments 7-1 to 7-10 were measured. The waterand isopropanol extraction results, diameter, base curve, oxygenpermeability, elongation, and refractive index of the lenses ofEmbodiments 7-1 to 7-10 are shown in Tables 8 to 10.

TABLE 8 Embodiment 7-1 7-2 siloxane compound 1 (Mn <800) 40 siloxanecompound 2 (Mn ~1000) 40 DMA 25 25 HEAA  5  5 NVP 30 25 bisacrylate (2)  0.6   0.6 acrylic acid  1  1 TAIC   0.1   0.1 TPO   0.1   0.1 RB-19   0.02    0.02 tert-amyl alcohol 15 15 UV energy (mJ/cm²)  35→133 35→133 time (min) 4→4 4→4 weight ratio of isopropanol extracts 5.49%1.56% diameter (mm)   14.29   14.49 base curve (mm)    8.39    8.86oxygen permeability (Dk) 63 61 elongation (%)  320%  348% refractiveindex     1.4022     1.4017

TABLE 9 Embodiment 7-3 7-4 7-5 7-6 siloxane compound 3 (Mn ~820) 40  40   40   40   DMA 25   25   20   20   HEAA 5   5   10   10   NVP 30  30   30   30   bisacrylate (2) 0.6 0.6 0.6 0.6 acrylic acid 1   1   TAIC0.1 0.1 0.1 0.1 TPO 0.3 0.3 0.3 0.3 RB-19  0.02  0.02  0.02  0.02tert-amyl alcohol 5   5   5   5   UV energy (mJ/cm²)  30→132  30→132 30→132  30→132 time (min) 8→8 8→8 8→8 10→10 weight ratio of waterextracts 1.01% 0.58% 1.05% 0.63% weight ratio of isopropanol extracts2.05% 1.53% 1.98% 1.85% oxygen permeability (Dk) 57.52 59.10 60.20 62.21elongation (%)  295%  335%  263%  287% refractive index   1.4195  1.4240   1.4220   1.4291

TABLE 10 Embodiment 7-7 7-8 7-9 7-10 siloxane compound 4 (Mn ~1200) 40 55 5 siloxane compound 1 (Mn <800) 35 30 siloxane compound 2 (Mn ~1000)35 DMA 25 25 25 30 HEAA 5 5 5 5 NVP 30 30 30 30 bisacrylate (2) 0.6 0.60.6 0.6 acrylic acid 1 1 1 1 TAIC 0.1 0.1 0.1 0.1 TPO 0.1 0.1 0.1 0.1RB-19 0.02 0.02 0.02 0.02 tert-amyl alcohol 15 15 15 15 UV energy(mJ/cm²)  30→132  30→132  30→132  30→132 time (min) 4→4 6→6 6→6 4→4weight ratio of isopropanol extracts 0.88% 0.6% 2.40% 0.87% diameter(mm) 12.9 14.48 14.38 14.86 base curve (mm) 7.69 8.64 8.55 8.6 oxygenpermeability (Dk) not 98.75 83.21 not measured measured elongation (%)low 280 288 250 refractive index 1.4351 1.4046 1.4022 1.4016

It can be seen from Table 8 that the lenses containing differentsiloxane compounds with different number average molecular weights hadsimilar properties (e.g., oxygen permeability, elongation, andrefractive index, etc.), but the lens containing the siloxane compoundwith higher number average molecular weight had higher weight ratio ofthe isopropanol extracts, indicating that the lens containing thesiloxane compound with higher number average molecular weight had lowercuring efficiency.

It can be seen from Table 9 that compared with the lens containing thesiloxane compound 1 capped with the acrylamide groups, the lensescontaining the siloxane compound 3 capped with the acryloyloxy groupshad very low weight ratios of the water extracts and those of theisopropanol extracts.

As can be seen from Table 10 that the lens made from the siliconehydrogel composition of Embodiments 7-7 includes the siloxane compound 4capped with the acryloyloxy groups was a hard lens. The lens ofEmbodiment 7-7 had low elongation and a small diameter compared with thelenses of Embodiments 7-8 to 7-10. From Embodiments 7-8 to 7-10, it isunderstood that compared with the silicone hydrogel compositioncontaining the siloxane compound 2 having the large number averagemolecular weight, the lenses made from the silicone hydrogelcompositions containing the siloxane compound 1 having the small numberaverage molecular weight had the low weight ratios of the isopropanolextracts.

Comparison of Lenses Including and Excluding Methacrylate MonomersEmbodiment 8-1

40 parts by weight of 3-tris(trimethyl siloxy) silylpropyl acrylamide(TRISAm), 25 parts by weight of N,N-dimethylacrylamide (DMA), 5 parts byweight of 2-hydroxyethyl methacrylate (HEMA), 30 parts by weight ofN-vinyl pyrrolidone (NVP), 0.4 parts by weight of trimethylpropyltrimethacrylate (TMPTMA), 0.1 parts by weight 1,3,5-triallylisocyanurate (TAIC), 0.3 parts by weight of TPO photoinitiator, 0.02parts by weight of a blue colorant (RB-19), and 5 parts by weight oftert-amyl alcohol were mixed to form a silicone hydrogel composition.Next, the silicone hydrogel composition was filled into a cavity of apolypropylene mold, and ultraviolet light of 30 mJ/cm² was applied for 8minutes to carry out a first photocuring reaction. Subsequently,ultraviolet light of 132 mJ/cm² was applied for 8 minutes to carry out asecond photocuring reaction to form a lens.

Embodiment 8-2

In this embodiment, the same components as in Embodiment 8-1 in additionto 0.4 parts by weight of TMPTMA replaced by 0.6 parts by weight ofethylene glycol dimethacrylate (EGDMA) were mixed to form a siliconehydrogel composition. Next, the silicone hydrogel composition was filledinto a cavity of a polypropylene mold, and ultraviolet light of 30mJ/cm² was applied for 8 minutes to carry out a first photocuringreaction. Subsequently, ultraviolet light of 132 mJ/cm² was applied for8 minutes to carry out a second photocuring reaction to form a lens.

Embodiment 8-3

In this embodiment, the same components as in Embodiment 8-1 in additionto 25 parts by weight of DMA replaced by 20 parts by weight of DMA, 5parts by weight of HEMA replaced by 10 parts by weight of HEMA, and 30parts by weight of NVP replaced by 25 parts by weight of NVP, andadditionally added 5 parts by weight of poly(ethylene glycol)methacrylate (PEGMA) were mixed to form a silicone hydrogel composition.Next, the silicone hydrogel composition was filled into a cavity of apolypropylene mold, and ultraviolet light of 30 mJ/cm² was applied for10 minutes to carry out a first photocuring reaction. Subsequently,ultraviolet light of 132 mJ/cm² was applied for 10 minutes to carry outa second photocuring reaction to form a lens.

Embodiment 8-4

In this embodiment, the same components as in Embodiment 8-1 in additionto 5 parts by weight of HEMA replaced by 5 parts by weight of2-hydroxyethyl acrylamide (HEAA), and 0.4 parts by weight of TMPTMAreplaced by 0.6 parts by weight of ethylene glycol diacrylate(bisacrylate (2)) were mixed to form a silicone hydrogel composition.Next, the silicone hydrogel composition was filled into a cavity of apolypropylene mold, and ultraviolet light of 30 mJ/cm² was applied for 8minutes to carry out a first photocuring reaction. Subsequently,ultraviolet light of 132 mJ/cm² was applied for 8 minutes to carry out asecond photocuring reaction to form a lens.

Embodiment 8-5

In this embodiment, the same components as in Embodiment 8-4 in additionto 0.6 parts by weight of ethylene glycol diacrylate (bisacrylate (2))replaced by 0.4 parts by weight of trimethylolpropane triacrylate(triacrylate (3)) were mixed to form a silicone hydrogel composition.Next, the silicone hydrogel composition was filled into a cavity of apolypropylene mold, and ultraviolet light of 30 mJ/cm² was applied for 8minutes to carry out a first photocuring reaction. Subsequently,ultraviolet light of 132 mJ/cm² was applied for 8 minutes to carry out asecond photocuring reaction to form a lens.

Comparative Embodiment 1

In this embodiment, the same components as in Embodiment 8-1 in additionto 40 parts by weight of TRISAm replaced by 40 parts by weight of3-tris(trimethylsiloxy)silylpropyl methacrylate (TRIS) were mixed toform a silicone hydrogel composition. Next, the silicone hydrogelcomposition was filled into a cavity of a polypropylene mold, andultraviolet light of 30 mJ/cm² was applied for 8 minutes to carry out afirst photocuring reaction. Subsequently, ultraviolet light of 132mJ/cm² was applied for 8 minutes to carry out a second photocuringreaction to form a lens.

Comparative Embodiment 2

In this embodiment, the same components as in Comparative Embodiment 1in addition to 0.4 parts by weight of TMPTMA replaced by 0.6 parts byweight of EGDMA were mixed to form a silicone hydrogel composition.Next, the silicone hydrogel composition was filled into a cavity of apolypropylene mold, and ultraviolet light of 30 mJ/cm² was applied for 8minutes to carry out a first photocuring reaction. Subsequently,ultraviolet light of 132 mJ/cm² was applied for 8 minutes to carry out asecond photocuring reaction to form a lens.

Comparative Embodiment 3

In this Embodiment, the same components as in Comparative Embodiment 1in addition to 25 parts by weight of DMA replaced by 20 parts by weightof DMA, 5 parts by weight of HEMA replaced by 10 parts by weight ofHEMA, 30 parts by weight of NVP replaced by 25 parts by weight of NVP,and additionally added 5 parts by weight of poly(ethylene glycol)methacrylate (PEGMA) were mixed to form a silicone hydrogel composition.Next, the silicone hydrogel composition was filled into a cavity of apolypropylene mold, and ultraviolet light of 30 mJ/cm² was applied for10 minutes to carry out a first photocuring reaction. Subsequently,ultraviolet light of 132 mJ/cm² was applied for 10 minutes to carry outa second photocuring reaction to form a lens.

Next, the lenses of Embodiments 8-1 to 8-5 and Comparative Embodiments 1to 3 were taken out from the polypropylene molds, and the lenses wereextracted with water and isopropanol according to the methods describedabove to obtain weights of water extracts and those of isopropanolextracts. Further, oxygen permeability, elongation, and refractive indexof the lenses of Embodiments 8-1 to 8-5 and Comparative Embodiments 1 to3 were measured. The water and isopropanol extraction results, oxygenpermeability, elongation, and refractive index of the lenses ofEmbodiments 8-1 to 8-5 and Comparative Embodiments 1 to 3 are listed inTable 11 and Table 12 below.

TABLE 11 Embodiment 8-1 8-2 8-3 8-4 8-5 TRISAm 40   40   40   40   40  TRIS DMA 25   25   20   25   25   HEMA 5   5   10   HEAA 5   5   PEGMA5   NVP 30   30   25   30   30   TMPTMA 0.4 0.4 EGDMA 0.6 bisacrylate(2) 0.6 triacrylate (3) 0.4 TAIC 0.1 0.1 0.1 0.1 0.1 TPO 0.3 0.3 0.3 0.30.3 RB-19  0.02  0.02  0.02  0.02  0.02 tert-amyl alcohol 5   5   5  5   5   UV energy (mJ/cm²)  30→132  30→132  30→132  30→132  30→132 time(min) 8→8 8→8 10→10 8→8 8→8 weight ratio of water 2.13% 1.84% 1.95%1.05% 1.14% extracts weight ratio of 3.53% 2.25% 2.85% 1.98% 2.17%isopropanol extracts oxygen permeability (Dk) 56.17 50.52 58.21 57.3459.31 elongation (%)  398%  295%  405%  385%  375% refractive index  1.3864   1.3912   1.3886   1.3841   1.3897

TABLE 12 Comparative Embodiment 1 2 3 TRISAm TRIS 40   40   40   DMA25   25   20   HEMA 5   5   10   HEAA PEGMA 5   NVP 30   30   25  TMPTMA 0.4 0.4 EGDMA 0.6 bisacrylate (2) triacrylate (3) TAIC 0.1 0.10.1 TPO 0.3 0.3 0.3 RB-19  0.02  0.02  0.02 tert-amyl alcohol 5   5  5   UV energy (mJ/cm²)  30→132  30→132  30→132 time (min) 8→8 8→8 10→10weight ratio of water 4.67% 3.97% 4.29% extracts weight ratio ofisopropanol 14.21%  11.54%  13.80%  extracts oxygen permeability (Dk)54.98 47.25 56.76 elongation (%)  428%  256%  388% refractive index  1.3862  1.397  1.388

As can be seen from Tables 11 and 12, when TRIS was used as the siloxanecompound (Comparative Embodiments 1 to 3), the weight ratios of thewater extracts and those of the isopropanol extracts of the lenses weresignificantly increased. Steric hindrance of the methacrylate group inthe TRIS structure increased the energy required for the polymerizationof the compound, and thus the residual water extracts and theisopropanol extracts were increased after the silicone hydrogelcomposition was cured. Further, when ethylene glycol diacrylate(bisacrylate (2)) or trimethylolpropane triacrylate (triacrylate (3))was used as the crosslinking monomer (i.e., Embodiments 8-4 or 8-5), theweight ratio of the water extracts of the lens (less than 1.2%) and theweight ratio of the isopropanol extracts of the lens (less than 2.2%)were very low, indicating that the silicone hydrogel composition wascompletely cured.

Comparison of Contact Lenses of Present Disclosure and CommerciallyAvailable Contact Lenses

After the curing of the silicone hydrogel compositions of Embodiments5-3, 5-4, 6-2, and 7-2 were completed, the lenses were taken out fromthe polypropylene molds, and the lenses were extracted using water.Thereafter, the lenses were immersed in propylene blister filled withborate buffered saline or a phosphorate buffered saline having pH valueof 7.3 to 7.4, and then autoclaved at 121° C. for 30 minutes to preparecontact lenses.

To illustrate advantages of the contact lenses of the presentdisclosure, four commercially available contact lenses were purchasedfor comparison. Specifically, the four commercially available contactlenses are Delefilcon (Dailies Total 1) sold by Alcon, Somofilcon soldby cooper Vision, Unifilcon sold by Marshal Intergroup and Miacare soldby Benq Materials. The contact lenses made from Embodiments 5-3, 5-4,6-2 and 7-2 and the four commercially available contact lenses wereextracted with methanol, and weight ratios of methanol extracts wereobserved to evaluate the advantages and disadvantages of each contactlens.

In particular, the method of extracting the contact lenses usingmethanol was that the contact lenses were taken from the blisterpackages and placed in stirred deionized water for 5 hours. Next, thewater was removed and replaced with fresh deionized water and stirringwas continued for 5 hours. Replacing fresh deionized water was performedfor two times. Thereafter, the contact lenses were dried in an oven at105° C. for 16 hours. The dried contact lenses were taken out and placedin a desiccator, and a first dry weight of each contact lens wasmeasured after 30 minutes. Next, the contact lenses were immersed inmethanol for 4 hours. Subsequently, the contact lenses were placed in anoven to dry in the same manner, and a second dry weight of each contactlens was measured. The weight ratio of the methanol extracts is thedifference between the first dry weight and the second dry weightdivided by the first dry weight. The weight ratios of the methanolextracts of the contact lenses of the present disclosure and thecommercially available contact lenses are listed in Table 13 below. Inaddition, curing methods and extraction methods used in the preparationprocess of the contact lenses of the present disclosure and thecommercially available contact lenses are also listed in Table 13 below.

TABLE 13 contact lenses Embodiment Embodiment Embodiment Embodiment 5-35-4 6-2 7-2 curing photocuring photocuring photocuring photocuringmethod extraction water water water water method extraction extractionextraction extraction % methanol 2.61% 0.58%  1.72%   0% extractscontact Delefilcon Miacare Unifilcon Somofilcon lenses curingphotocuring photocuring photocuring thermal method curing extractionorganic organic water water method solvent solvent extraction extractionextraction extraction % methanol 0.90% 1.70% 10.50% 4.70% extracts

As can be seen from Table 13, the commercially available Delefilcon andMiacare contact lenses were prepared using the photocuring process andthe organic solvent extraction process. Therefore, the weight ratios ofthe methanol extracts of Delefilcon and Miacare contact lenses were low.However, it also means that the manufacturing costs of Delefilcon andMiacare contact lenses that required the organic solvent extractionprocess were very high.

On the other hand, the commercially available Unifilcon and Somofilconcontact lenses were prepared using the photocuring process and thethermal curing process, respectively, and water extraction processes.Since Unifilcon and Somofilcon contact lenses were only subjected to thewater extraction processes, the weight ratios of the methanol extractswere very high (10.50% and 4.70%). That is, Unifilcon and Somofilconcontact lenses contain a large amount of unreacted and non-crosslinkedsiloxane compounds, which may adversely affect the wearers (e.g.,reduced wettability and lipid deposition).

The contact lenses of Embodiments 5-3, 5-4, 6-2, and 7-2 were preparedonly using the water extraction processes, but the weight ratios of themethanol extracts were extremely low (less than 2.7%). The weight ratioof the methanol extracts of the contact lens of Embodiment 7-2 was even0%. It means that almost all of the siloxane compounds in the siliconehydrogel compositions of the present disclosure had been completelypolymerized without residue, so that the weight ratios of the methanolextracts of the produced contact lenses were extremely low.

In summary, the present disclosure provides a silicone hydrogelcomposition that can be used to prepare a contact lens. Since almost allof the siloxane compound has been completely polymerized without residueafter the silicone hydrogel composition of the present disclosure iscured, it is not necessary to use an organic solvent to wash the lensobtained by polymerization, thereby reducing the manufacturing cost ofthe contact lens.

While the disclosure has been disclosed above in the embodiments, otherembodiments are possible. Therefore, the spirit and scope of the claimsare not limited to the description contained in the embodiments herein.

It is apparent to those skilled in the art that various alterations andmodifications can be made without departing from the spirit and scope ofthe disclosure, and the scope of the disclosure is defined by the scopeof the appended claims.

What is claimed is:
 1. A method of manufacturing a silicone hydrogellens, comprising: providing a silicone hydrogel composition, wherein thesilicone hydrogel composition comprises: a first hydrophilic monomerhaving an acrylate functional group or an acrylamide functional group; asiloxane compound having an acrylate functional group or an acrylamidefunctional group; a first crosslinking monomer having a plurality ofacrylate functional groups or acrylamide functional groups; a secondhydrophilic monomer having a non-conjugated vinyl group; a secondcrosslinking monomer having a plurality of non-conjugated vinyl groups,wherein energy required for polymerization of the second hydrophilicmonomer and the second crosslinking monomer is higher than that of thefirst hydrophilic monomer, the siloxane compound, and the firstcrosslinking monomer; and a photoinitiator, wherein the photoinitiatorcomprises 1-hydroxycyclohexyl phenyl ketone, 2,4,6-trimethyl benzoyldiphenyl phosphine oxide, phenyl bis(2,4,6-trimethyl benzoyl)phosphineoxide, a combination of bis-(2,6-dimethoxy benzoyl)(2,4,4-trimethylpentyl) phosphine oxide and 1-hydroxycyclohexyl phenylketone, a combination of bis-(2,6-dimethoxy benzoyl)(2,4,4-trimethylpentyl) phosphine oxide and 2-hydroxy-2-methylpropiophenone, or a combination thereof; wherein a sum of a weight ofthe second hydrophilic monomer and a weight of the second crosslinkingmonomer is 40 to 100 parts by weight, relative to 100 parts by weight ofa sum of a weight of the first hydrophilic monomer, a weight of thesiloxane compound, and a weight of the first crosslinking monomer; andsequentially performing a first photocuring reaction and a secondphotocuring reaction on the silicone hydrogel composition to form thesilicone hydrogel lens, wherein energy applied in the second photocuringreaction is higher than energy applied in the first photocuringreaction.
 2. The method of claim 1, wherein the energy applied in thefirst photocuring reaction is less than 50 mJ/cm², and the energyapplied in the second photocuring reaction is higher than 100 mJ/cm². 3.The method of claim 1, wherein after performing the first photocuringreaction and the second photocuring reaction, further comprising:extracting the silicone hydrogel lens using an aqueous solution.
 4. Amethod of manufacturing a silicone hydrogel lens, comprising: providinga silicone hydrogel composition, wherein the silicone hydrogelcomposition comprises: a first hydrophilic monomer having an acrylatefunctional group or an acrylamide functional group; a siloxane compoundhaving an acrylate functional group or an acrylamide functional group,wherein the siloxane compound has a number average molecular weight ofless than 1200; a first crosslinking monomer having a plurality ofacrylate functional groups or acrylamide functional groups; a secondhydrophilic monomer having a non-conjugated vinyl group; a secondcrosslinking monomer having a plurality of non-conjugated vinyl groups,wherein energy required for polymerization of the second hydrophilicmonomer and the second crosslinking monomer is higher than that of thefirst hydrophilic monomer, the siloxane compound, and the firstcrosslinking monomer; and a photoinitiator, wherein the photoinitiatorcomprises 1-hydroxycyclohexyl phenyl ketone, 2,4,6-trimethyl benzoyldiphenyl phosphine oxide, phenyl bis(2,4,6-trimethyl benzoyl)phosphineoxide, a combination of bis-(2,6-dimethoxy benzoyl)(2,4,4-trimethylpentyl) phosphine oxide and 1-hydroxycyclohexyl phenylketone, a combination of bis-(2,6-dimethoxy benzoyl)(2,4,4-trimethylpentyl) phosphine oxide and 2-hydroxy-2-methylpropiophenone, or a combination thereof; wherein a sum of a weight ofthe second hydrophilic monomer and a weight of the second crosslinkingmonomer is 40 to 100 parts by weight, relative to 100 parts by weight ofa sum of a weight of the first hydrophilic monomer, a weight of thesiloxane compound, and a weight of the first crosslinking monomer; andsequentially performing a first photocuring reaction and a secondphotocuring reaction on the silicone hydrogel composition to form thesilicone hydrogel lens, wherein energy applied in the second photocuringreaction is higher than energy applied in the first photocuringreaction.
 5. A method of manufacturing a silicone hydrogel lens,comprising: providing a silicone hydrogel composition, wherein thesilicone hydrogel composition comprises: a first hydrophilic monomerhaving an acrylate functional group or an acrylamide functional group; asiloxane compound having an acrylate functional group or an acrylamidefunctional group, wherein the siloxane compound has a number averagemolecular weight of less than 800; a first crosslinking monomer having aplurality of acrylate functional groups or acrylamide functional groups;a second hydrophilic monomer having a non-conjugated vinyl group; asecond crosslinking monomer having a plurality of non-conjugated vinylgroups, wherein energy required for polymerization of the secondhydrophilic monomer and the second crosslinking monomer is higher thanthat of the first hydrophilic monomer, the siloxane compound, and thefirst crosslinking monomer; and a photoinitiator, wherein thephotoinitiator comprises 1-hydroxycyclohexyl phenyl ketone,2,4,6-trimethyl benzoyl diphenyl phosphine oxide, phenylbis(2,4,6-trimethyl benzoyl)phosphine oxide, a combination ofbis-(2,6-dimethoxy benzoyl) (2,4,4-trimethylpentyl) phosphine oxide and1-hydroxycyclohexyl phenyl ketone, a combination of bis-(2,6-dimethoxybenzoyl) (2,4,4-trimethylpentyl) phosphine oxide and 2-hydroxy-2-methylpropiophenone, or a combination thereof; wherein a sum of a weight ofthe second hydrophilic monomer and a weight of the second crosslinkingmonomer is 40 to 100 parts by weight, relative to 100 parts by weight ofa sum of a weight of the first hydrophilic monomer, a weight of thesiloxane compound, and a weight of the first crosslinking monomer; andsequentially performing a first photocuring reaction and a secondphotocuring reaction on the silicone hydrogel composition to form thesilicone hydrogel lens, wherein energy applied in the second photocuringreaction is higher than energy applied in the first photocuringreaction.
 6. The method of claim 1, wherein the siloxane compound is ina range of 35 wt % to 60 wt % based on a total weight of the siliconehydrogel composition.
 7. The method of claim 1, wherein the siloxanecompound has a structure of a following formula (1):

wherein X is O or NH; L is (CH₂)_(m), (CH₂)_(m)—[O(CH₂)_(p)]_(q) or(CH₂)_(m)(CHOH)—[O(CH₂)_(p)]_(q); R₁ is OH, CH₃ or OSi(CH₃)₃; R₂ is CH₃or OSi(CH₃)₃; R₃ is an alkyl group; n is an integer from 1 to 30; m andp are integers from 2 to 5; and q is an integer from 1 to
 5. 8. Themethod of claim 1, wherein the siloxane compound is a siloxane monomer,a siloxane macromonomer or a siloxane prepolymer.
 9. The method of claim1, wherein the siloxane compound comprises 3-tris(trimethyl siloxy)silylpropyl acrylamide, 3-tris(trimethyl siloxy) silylpropyl acrylate,3-tris(triethyl siloxy) silylpropyl acrylamide, 3-tris(triethyl siloxy)silylpropyl acrylate, (3-acryloxy-2-hydroxy propoxy) propylbis(trimethyl siloxy) methyl silane, (3-acryloxy-2-hydroxy propoxy)propyl bis(trimethyl siloxy) ethyl silane, (3-acrylamido-2-hydroxypropoxy) propyl bis(trimethyl siloxy)methyl silane,(3-acrylamido-2-hydroxy propoxy) propyl bis(trimethyl siloxy)ethylsilane, α-acrylamidopropyl-ω-butyl polydimethylsiloxane, α-acrylamidoethoxypropyl-ω-butyl polydimethylsiloxane, α-acryloxybutyl-ω-butylpolydimethylsiloxane, α-acryloxypropyl-ω-butyl polydimethylsiloxane,α-acryloxyethoxypropyl-ω-butyl polydimethylsiloxane, bis-α, ω-acrylamidopropyl polydimethylsiloxane, bis-α,ω-acrylamidoethoxypropylpolydimethylsiloxane, bis-α,ω-acryloxybutyl polydimethylsiloxane,bis-α,ω-acryloxypropyl polydimethylsiloxane,bis-α,ω-acryloxyethoxypropyl polydimethylsiloxane, or a combinationthereof.
 10. The method of claim 1, wherein the first hydrophilicmonomer is in a range of 10 wt % to 40 wt % based on a total weight ofthe silicone hydrogel composition.
 11. The method of claim 1, whereinthe first hydrophilic monomer is selected from the group comprising2-hydroxyethyl acrylamide, glycerol acrylate, acrylic acid,N,N-dimethylacrylamide, hydroxyethyl acrylamide,2-acrylamido-2-methylpropanesulfonic acid, or a combination thereof. 12.The method of claim 1, wherein the first crosslinking monomer is in arange of 0.1 wt % to 5 wt % based on a total weight of the siliconehydrogel composition.
 13. The method of claim 1, wherein the firstcrosslinking monomer is selected from the group comprisingtrimethylpropyl trimethacrylate, ethylene glycol diacrylate, diethyleneglycol diacrylate, triethylene glycol diacrylate, trimethylolpropanetriacrylate, pentaerythritol tetra acrylate, tetraethylene glycoldiacrylate, polyethylene glycol diacrylate, ethylene diacrylamide,butylene 1,4-diacrylamide, or a combination of thereof.
 14. The methodof claim 1, wherein the second hydrophilic monomer is in a range of 20wt % to 50 wt % based on a total weight of the silicone hydrogelcomposition.
 15. The method of claim 1, wherein the second hydrophilicmonomer is selected from the group comprising N-vinyl pyrrolidone,1-vinylazonan-2-one, N-vinyl-N-methyl acetamide, vinyl sulfonic acid,glycine vinyl carbamate, glycine vinyl carbonate, or a combinationthereof.
 16. The method of claim 1, wherein the second crosslinkingmonomer is in a range of 0.01 wt % to 1 wt % based on a total weight ofthe silicone hydrogel composition.
 17. The method of claim 1, whereinthe second crosslinking monomer is 1,3,5-triallyl isocyanurate.
 18. Themethod of claim 1, wherein at least one of the first hydrophilicmonomer, the siloxane compound, and the first crosslinking monomercomprises a methacrylate group or a methacrylamide group and is in arange of less than or equal to 20 wt % based on a total weight of thesilicone hydrogel composition.
 19. The method of claim 1, wherein thesilicone hydrogel lens is free of extraction using an organic solventafter the second photocuring reaction.